42015-36-1Relevant academic research and scientific papers
3-Deoxypentosulose: An α-dicarbonyl compound predominating in nonenzymatic browning of oligosaccharides in aqueous solution
Hollnagel, Anke,Kroh, Lothar W.
, p. 1659 - 1664 (2002)
The thermal degradation of D-glucose, maltose, and maltotriose in aqueous solution was investigated under caramelization (no glycine) and Maillard (with glycine) conditions. Degradation of the sugar and α-dicarbonyls product was monitored. Under both caramelization and Maillard reaction conditions, 3-deoxypentosulose was the predominating α-dicarbonyl compound formed from maltose and maltotriose. In the absence of an amino compound, however, 3-deoxypentosulose is formed in much lower concentration. It was concluded that 3-deoxypentosulose is formed by a pathway specific for oligo- and polysaccharides since this α-dicarbonyl is formed from the α-1→4 glucans such as maltose and maltotriose but not from glucose. For its formation, a retro Claisen reaction of an enolization product of 1-amino-1,4-dideoxyhexosulose is proposed as the route to its formation. 1-Amino-1,4-dideoxyhexosulose could be formed by vinylogous α-elimination from the 2,3-enediol structure after Amadori rearrangement, favored by planar alignment of the bonds between C1 and C4. Subsequent rearrangement by keto - enoltautomerization leads to a 1-imino-3-keto structure. In this structure, attack of a hydroxyl anion, provided by water at neutral pH, could cause a splitting off of the C1. This reaction gives rise to formic acid or formamide and a pentose derivative, which reacts further to give 3-deoxypentosulose.
Formation of α-dicarbonyl compounds in beer during storage of pilsner
Bravo, Adriana,Herrera, Julio C.,Scherer, Erika,Ju-Nam, Yon,Ruebsam, Heinrich,Madrid, Jorge,Zufall, Carsten,Rangel-Aldao, Rafael
experimental part, p. 4134 - 4144 (2010/03/31)
With the aim of determining the formation of α-dicarbonyl intermediates during beer aging on the shelf, α-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of α-dicarbonyls
Structural Changes of Quinoxaline Derivatives, with Special Reference to 2-(2',3'-Dihydroxypropyl)-3-hydroxymethylquinoxaline in Alakaline and Acidic Solutions
Morita, Naofumi,Inoue, Keiichi,Hayashi, Hideo,Takagi, Masanosuke
, p. 2053 - 2060 (2007/10/02)
Conversion products of 2-(2',3'-dihydroxypropyl)-3-hydroxymethylquinoxaline under alkaline and acidic refluxed conditions were characterized using GLC, GC-MS, HPLC, and NMR measurements.In an alkaline solution (pH 10, carbonate buffer), 2-(2',3'-dihydroxypropyl)-3-methylquinoxaline (GA-1) and 2-(2',3'-dihydroxypropyl)quinoxaline were produced in yields of 16percent and 19percent, respectively, whereas in an acidic solution (MeOH-AcOH-H2O=4:5:2), a large amount (65percent) of 3,4-dihydro-1H-pyranoquinoxalin-3-yl methanol and a small amount (5percent) of GA-1 were obtained.These results suggest that the C-C linkage of the side chain in the quinoxaline readily splits in alkaline solutions, whereas in acidic solutions no such splitting can be observed, but condensation or dehydration occurs between hydroxyl groups of the side chains, or the hydroxymethyl group is reduced to a methyl group.
Quinoxalines Derived from D-Galactose and o-Phenylenediamine in Acidic Media
Morita, Naofumi,Inoue, Keiichi,Takagi, Masanosuke
, p. 1329 - 1332 (2007/10/02)
Quinoxalines derived from D-galactose with o-phenylenediamine (OPD) in acidic media under reflux were studied by using GLC and NMR measurements.Four quinoxaline derivatives were obtained from the reaction mixture, and were identical with those derived from D-glucose.The yields of 2-(D-lyxo-tetrahydroxybutyl)quinoxaline (GA-III), and the stereoisomeric derivative of GA-III, i.e., 2-(D-arabino-tetrahydroxybutyl)quinoxaline (ATBQ), were 13.2 and 5.3percent, respectively.The ratio of GA-III to ATBQ derived from D-galactose was reciprocally coincident with that from D-glucose.Some proposals are made on the relationship between the isomerization of these sugars and the formation of quinoxaline derivatives.
